US20140296280A1 - Pures-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1h,-5h-benzo[i,j]quinolizine-2- carboxylic acid l-arginine salt tetrahydrate and a process for its preparation - Google Patents
Pures-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1h,-5h-benzo[i,j]quinolizine-2- carboxylic acid l-arginine salt tetrahydrate and a process for its preparation Download PDFInfo
- Publication number
- US20140296280A1 US20140296280A1 US14/240,400 US201214240400A US2014296280A1 US 20140296280 A1 US20140296280 A1 US 20140296280A1 US 201214240400 A US201214240400 A US 201214240400A US 2014296280 A1 US2014296280 A1 US 2014296280A1
- Authority
- US
- United States
- Prior art keywords
- quinolizine
- benzo
- dihydro
- oxo
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000002158 endotoxin Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 5
- 229930064664 L-arginine Natural products 0.000 claims description 5
- 235000014852 L-arginine Nutrition 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- JYJTVFIEFKZWCJ-JTQLQIEISA-N C[C@H]1CCC2=C(N3CCC(O)CC3)C(F)=CC3=C2N1C=C(C(=O)O)C3=O Chemical compound C[C@H]1CCC2=C(N3CCC(O)CC3)C(F)=CC3=C2N1C=C(C(=O)O)C3=O JYJTVFIEFKZWCJ-JTQLQIEISA-N 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- -1 salt tetrahydrate Chemical class 0.000 description 1
- IXGNPUSUVRTQGW-UHFFFAOYSA-M sodium;perchlorate;hydrate Chemical compound O.[Na+].[O-]Cl(=O)(=O)=O IXGNPUSUVRTQGW-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the invention relates to substantially pure S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate and a process for its preparation.
- the compound of Formula (I) chemically known as S-( ⁇ )-9-fluoro-8-(4-hydroxy piperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, belongs to a class of antibacterial agents generally known as fluoroquinolones and is useful in treating a broad range of bacterial infections.
- U.S. Pat. No. 7,164,023 discloses a crystalline S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate and its preparation.
- the present invention is directed to a substantially pure S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate and a process for its preparation.
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.5% w/w of R-(+)-9-fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, as determined by HPLC.
- composition comprising S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate according to the invention.
- step (c) warming the solution obtained in step (b) to get a clear solution
- step (d) optionally treating the warm solution obtained in step (c) with activated carbon and filtering the treated solution;
- step (e) diluting the warm solution obtained in step (d) with acetone and refluxing the diluted solution;
- step (f) cooling the solution obtained in step (e) to obtain solid S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate;
- step (g) collecting S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate obtained in step (f) by filtration, and optionally washing it with acetone.
- the invention provides substantially pure S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate and a process for its preparation.
- substantially pure S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate refers to S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having one or more of the following specifications:
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.15% w/w of 9-fluoro-8-hydroxy-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, as determined by HPLC.
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.15% w/w of 8-fluoro-9-(4-hydroxy-piperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, as determined by HPLC.
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.15% w/w of 8-(4-hydroxy-1-piperidinyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, as determined by HPLC.
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.15% w/w of 8,9-difluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, determined by HPLC.
- S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate having a purity of at least 99% w/w, further containing less than 0.5% w/w of R-(+)-9-fluoro-8-(4-hydroxy-piperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, as determined by HPLC.
- step (c) warming the solution obtained in step (b) to get a clear solution
- step (d) optionally treating the warm solution obtained in step (c) with activated carbon and filtering the treated solution;
- step (e) diluting the warm solution obtained in step (d) with acetone and refluxing the diluted solution;
- step (f) cooling the solution obtained in step (e) to obtain solid S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate;
- step (g) collecting S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate obtained in step (f) by filtration, and optionally washing it with acetone.
- a pharmaceutical composition comprising substantially pure S-( ⁇ )-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,-5H-benzo[i,j]quinolizine-2-carboxylic acid L-arginine salt tetrahydrate according to the invention.
- compositions according to the invention may further comprise one or more pharmaceutically acceptable excipients.
- the content of other substances (Table 1, Sr. No. 1 to 5) in the product was determined using HPLC (Waters 2695 separation module or equivalent).
- HPLC Waters 2695 separation module or equivalent.
- the HPLC column having 150 mm length and 4.6 mm ID packed with 3.5 ⁇ particles of X-Terra RP18 was used.
- Mobile phase A used was a mixture of ammonium acetate (3.0 gm) and sodium perchlorate monohydrate (8.4 gm) in 1000 ml of HPLC grade water with final pH adjusted to 2.2 with orthophosphoric acid.
- Mobile phase B was mixture of methanol and acetonitrile in ratio of 60:40, v/v. Mobile phase was run in gradient mode.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN270/MUM/2011 | 2011-09-28 | ||
| IN2740MU2011 | 2011-09-28 | ||
| PCT/IB2012/050074 WO2013046061A1 (en) | 2011-09-28 | 2012-01-06 | Pures-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1h,-5h-benzo[i,j]quinolizine-2- carboxylic acid l-arginine salt tetrahydrate and a process for its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20140296280A1 true US20140296280A1 (en) | 2014-10-02 |
Family
ID=45498072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/240,400 Abandoned US20140296280A1 (en) | 2011-09-28 | 2012-01-06 | Pures-(-)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1h,-5h-benzo[i,j]quinolizine-2- carboxylic acid l-arginine salt tetrahydrate and a process for its preparation |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20140296280A1 (es) |
| EP (1) | EP2776433A1 (es) |
| JP (1) | JP6126102B2 (es) |
| KR (1) | KR20140054307A (es) |
| CN (1) | CN103842361A (es) |
| AU (1) | AU2012313987B2 (es) |
| BR (1) | BR112014006401A2 (es) |
| CA (1) | CA2850159A1 (es) |
| MX (1) | MX366887B (es) |
| RU (1) | RU2594166C2 (es) |
| WO (1) | WO2013046061A1 (es) |
| ZA (1) | ZA201401262B (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180325879A1 (en) * | 2017-04-14 | 2018-11-15 | Wockhardt Limited | Antibacterial compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6664267B1 (en) * | 2002-05-28 | 2003-12-16 | Wockhardt Limited | Crystalline fluoroquinolone arginine salt form |
| WO2005023805A1 (en) * | 2003-09-04 | 2005-03-17 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7247642B2 (en) * | 1999-05-07 | 2007-07-24 | Wockhardt Limited | Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment |
| DE60131416T2 (de) * | 2000-05-08 | 2008-09-18 | Wockhardt Ltd. | Chirale fluochinolon-argininsalzformen |
| ZA200807674B (en) * | 2006-03-07 | 2009-11-25 | Wockhardt Ltd | Prodrugs of benzoquinolizine-2-carboxylic acid |
-
2012
- 2012-01-06 WO PCT/IB2012/050074 patent/WO2013046061A1/en not_active Ceased
- 2012-01-06 CN CN201280047235.5A patent/CN103842361A/zh active Pending
- 2012-01-06 JP JP2014532505A patent/JP6126102B2/ja active Active
- 2012-01-06 AU AU2012313987A patent/AU2012313987B2/en not_active Ceased
- 2012-01-06 EP EP12700532.0A patent/EP2776433A1/en not_active Withdrawn
- 2012-01-06 KR KR1020147007356A patent/KR20140054307A/ko not_active Ceased
- 2012-01-06 RU RU2014115989/04A patent/RU2594166C2/ru active IP Right Revival
- 2012-01-06 US US14/240,400 patent/US20140296280A1/en not_active Abandoned
- 2012-01-06 BR BR112014006401A patent/BR112014006401A2/pt not_active Application Discontinuation
- 2012-01-06 MX MX2014003770A patent/MX366887B/es active IP Right Grant
- 2012-01-06 CA CA2850159A patent/CA2850159A1/en not_active Abandoned
-
2014
- 2014-02-19 ZA ZA2014/01262A patent/ZA201401262B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6664267B1 (en) * | 2002-05-28 | 2003-12-16 | Wockhardt Limited | Crystalline fluoroquinolone arginine salt form |
| WO2005023805A1 (en) * | 2003-09-04 | 2005-03-17 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
| US7164023B2 (en) * | 2003-09-04 | 2007-01-16 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
Non-Patent Citations (1)
| Title |
|---|
| Yeole R. et al , 2006, Validated Chiral HPLC method for novel anti-methyicillin- resistant Staphylococcus aureus fluoroquinoline WCK 771. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180325879A1 (en) * | 2017-04-14 | 2018-11-15 | Wockhardt Limited | Antibacterial compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2012313987A1 (en) | 2014-03-06 |
| MX2014003770A (es) | 2014-04-30 |
| RU2594166C2 (ru) | 2016-08-10 |
| JP2014527998A (ja) | 2014-10-23 |
| ZA201401262B (en) | 2015-10-28 |
| AU2012313987B2 (en) | 2016-11-24 |
| NZ621358A (en) | 2016-03-31 |
| JP6126102B2 (ja) | 2017-05-10 |
| CA2850159A1 (en) | 2013-04-04 |
| RU2014115989A (ru) | 2015-11-10 |
| EP2776433A1 (en) | 2014-09-17 |
| BR112014006401A2 (pt) | 2017-03-28 |
| WO2013046061A1 (en) | 2013-04-04 |
| MX366887B (es) | 2019-07-29 |
| KR20140054307A (ko) | 2014-05-08 |
| CN103842361A (zh) | 2014-06-04 |
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